IP Library Granted Patent US 8,008,317
Granted Patent B2
US 8,008,317 · App. 11/921,352 · Granted Aug 30, 2011

Inhibitors of akt activtiy

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Quick Facts
Patent No.
US 8,008,317
App. No.
11/921,352
Granted
Aug 30, 2011
Kind
B2
Abstract

The instant invention provides for substituted naphthyridine compounds that inhibit Akt activity. In particular, the compounds disclosed selectively inhibit one or two of the Akt isoforms. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting Akt activity by administering the compound to a patient in need of treatment of cancer.

Claims (276)

1. A compound according to Formula E:

wherein:

a is 0 or 1; b is 0 or 1; m is 0, 1 or 2;

the dashed line represents an optional double bond;

R 1 is selected from: H, oxo, (C═O) a O b (C 1 -C 10 )alkyl, (C═O) a O b -aryl, (C═O) a O b (C 2 -C 10 )alkenyl, (C═O) a O b (C 2 -C 10 )alkynyl, CO 2 H, halo, OH, O b (C 1 -C 6 )perfluoroalkyl, (C═O) a NR 7 R 8 , CN, (C═O) a O b (C 3 -C 8 )cycloalkyl, S(O) m NR 7 R 8 , SH, S(O) m —(C 1 -C 10 )alkyl and (C═O) a O b -heterocyclyl, said alkyl, aryl, alkenyl, alkynyl, cycloalkyl, and heterocyclyl is optionally substituted with one or more substituents selected from R 6 ;

R 3 is selected from: H, oxo, (C═O) a O b (C 1 -C 10 )alkyl, (C═O) a O b -aryl, (C═O) a O b (C 2 -C 10 )alkenyl, (C═O) a O b (C 2 -C 10 )alkynyl, CO 2 H, halo, OH, O b (C 1 -C 6 )perfluoroalkyl, (C═O) a NR 7 R 8 , CN, (C═O) a O b (C 3 -C 8 )cycloalkyl, S(O) m NR 7 R 8 , SH, S(O) m —(C 1 -C 10 )alkyl, (C 1 -C 6 )alkyl-heterocyclyl and (C═O) a O b -heterocyclyl, said alkyl, aryl, alkenyl, alkynyl, cycloalkyl, and heterocyclyl is optionally substituted with one or more substituents selected from R 6 ;

R 6 is: (C═O) a O b C 1 -C 10 alkyl, (C═O) a O b aryl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, (C═O) a O b heterocyclyl, CO 2 H, halo, CN, OH, O b C 1 -C 6 perfluoroalkyl, O a (C═O) b NR 7 R 8 , oxo, CHO, (N═O)R 7 R 8 , S(O) m NR 7 R 8 , SH, S(O) m —(C 1 -C 10 )alkyl or (C═O) a O b C 3 -C 8 cycloalkyl, said alkyl, aryl, alkenyl, alkynyl, heterocyclyl, and cycloalkyl optionally substituted with one or more substituents selected from R 6a ;

R 6a is selected from: (C═O) a O b (C 1 -C 10 )alkyl, O a (C 1 -C 3 )perfluoroalkyl, (C 0 -C 6 )alkylene-S(O) m R a ; SH, oxo, OH, halo, CN, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, (C 3 -C 6 )cycloalkyl, (C 0 -C 6 )alkylene-aryl, (C 0 -C 6 )alkylene-heterocyclyl, (C 0 -C 6 )alkylene-N(R b ) 2 , C(O)R a , (C 0 -C 6 )alkylene-CO 2 R a , C(O)H, and (C 0 -C 6 )alkylene-CO 2 H, said alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heterocyclyl is optionally substituted with up to three substituents selected from R b , OH, (C 1 -C 6 )alkoxy, halogen, CO 2 H, CN, O a (C═O) b (C 1 -C 6 )alkyl, oxo, and N(R b ) 2 ;

R 7 and R 8 are independently selected from: H, (C═O) a O b (C 1 -C 10 )alkyl, (C═O) a O b (C 3 -C 8 )cycloalkyl, (C═O) a O b -aryl, (C═O) a O b -heterocyclyl, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, SH, SO 2 R a , and (C═O) a NR b 2 , said alkyl, cycloalkyl, aryl, heterocylyl, alkenyl, and alkynyl is optionally substituted with one or more substituents selected from R 6a , or R 7 and R 8 can be taken together with the nitrogen to which they are attached to form a monocyclic or bicyclic heterocycle with 3-7 members in each ring and optionally containing, in addition to the nitrogen, one or two additional heteroatoms selected from N, O and S, said monocyclic or bicyclic heterocycle optionally substituted with one or more substituents selected from R 6a ;

R a is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, aryl, or heterocyclyl; and

R b is independently: H, (C 1 -C 6 )alkyl, aryl, heterocyclyl, (C 3 -C 6 )cycloalkyl, (C═O) a O b (C 1 -C 6 )alkyl, or S(O) m R a ;

or a pharmaceutically acceptable salt, tautomer, or a stereoisomer thereof.

2. A compound according to Formula J:

wherein:

a is 0 or 1; b is 0 or 1; m is 0, 1 or 2;

the dashed line represents an optional double bond;

R 1 is selected from: CF 3 , H, oxo, (C═O) a O b (C 1 -C 10 )alkyl, (C═O) a O b-aryl, (C═O) a O b (C 2 -C 10 )alkenyl, (C═O) a O b (C 2 -C 10 )alkynyl, CO 2 H, halo, OH, O b (C 1 -C 6 )perfluoroalkyl, (C═O) a NR 7 R 8 , CN, (C═O) a O b (C 3 -C 8 )cycloalkyl, S(O) m NR 7 R 8 , SH, S(O) m —(C 1 -C 10 )alkyl and (C═O) a O b -heterocyclyl, said alkyl, aryl, alkenyl, alkynyl, cycloalkyl, and heterocyclyl is optionally substituted with one to six substituents selected from R 6 ;

R 3′ and R 3″ are independently selected from: CF 3 , H, oxo, (C═O) a O b (C 1 -C 10 )alkyl, (C═O) a O b -aryl, (C═O) a O b (C 2 -C 10 )alkenyl, (C═O) a O b (C 2 -C 10 )alkynyl, CO 2 H, halo, OH, O b (C 1 -C 6 )perfluoroalkyl, (C═O) a NR 7 R 8 , CN, (C═O) a O b (C 3 -C 8 )cycloalkyl, S(O) m NR 7 R 8 , SH, S(O) m —(C 1 -C 10 )alkyl, (C 1 -C 6 )alkyl-heterocyclyl and (C═O) a O b -heterocyclyl, said alkyl, aryl, alkenyl, alkynyl, cycloalkyl, and heterocyclyl is optionally substituted with one to five substituents selected from R 6 ; or R 3′ and R 3″ can be taken together with the nitrogen to which they are attached to form a piperidine or pyrrolidine which may be optionally substituted with one to five substituents selected from R 6 ;

R 4 and R 5 are independently: H, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkenyl, (C 1 -C 6 )alkynyl, wherein said alkyl is optionally substituted with up to three substituents selected from: OH and halo; and wherein R 4 and R 5 can be taken together to form a (C 3 -C 7 )cycloalkyl, wherein said cycloalkyl is optionally substituted with up to three substituents selected from R 6 ;

R 6 is: CF 3 , (C═O) a O b C 1 -C 10 alkyl, (C═O) a O b aryl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, (C═O) a O b heterocyclyl, CO 2 H, halo, CN, OH, O b C 1 -C 6 perfluoroalkyl, O a (C═O) b NR 7 R 8 , oxo, CHO, (N═O)R 7 R 8 , S(O) m NR 7 R 8 , SH, S(O) m —(C 1 -C 10 )alkyl or (C═O) a O b C 3 -C 8 cycloalkyl, said alkyl, aryl, alkenyl, alkynyl, heterocyclyl, and cycloalkyl optionally substituted with one to five substituents selected from R 6a ;

R 6a is selected from: CF 3 , (C═O) a O b (C 1 -C 10 )alkyl, O a (C 1 -C 3 )perfluoroalkyl, (C 0 -C 6 )alkylene-S(O) m R a , SH, oxo, OH, halo, CN, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, (C 3 -C 6 )cycloalkyl, (C 0 -C 6 )alkylene-aryl, (C 0 -C 6 )alkylene-heterocyclyl, (C 0 -C 6 )alkylene-N(R b ) 2 , (C═O) a NR b 2 , C(O)R a , (C 0 -C 6 )alkylene-CO 2 R a , C(O)H, and (C 0 -C 6 )alkylene-CO 2 H, said alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heterocyclyl is optionally substituted with up to three substituents selected from R b , OH, (C 1 -C 6 )alkoxy, halogen, CO 2 H, CN, O a (C═O) b (C 1 -C 6 )alkyl, oxo, and N(R b ) 2 ;

R 7 and R 8 are independently selected from: CF 3 , H, (C═O) a O b (C 1 -C 10 )alkyl, (C═O) a O b (C 3 -C 8 )cycloalkyl, (C═O) a O b -aryl, (C═O) a O b -heterocyclyl, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, SH, SO 2 R a , and (C═O) a NR b 2 , said alkyl, cycloalkyl, aryl, heterocylyl, alkenyl, and alkynyl is optionally substituted with one to five substituents selected from R 6a , or R 7 and R 8 can be taken together with the nitrogen to which they are attached to form a monocyclic or bicyclic heterocycle with 3-7 members in each ring and optionally containing, in addition to the nitrogen, one or two additional heteroatoms selected from N, O and S, said monocyclic or bicyclic heterocycle optionally substituted with one to six substituents selected from R 6a ;

R a is (C 1 -C 6 )alkyl, NR b 2 , (C 3 -C 6 )cycloalkyl, aryl, or heterocyclyl; and

R b is independently: H, (C 1 -C 6 )alkyl, NH 2 , aryl, heterocyclyl, (C 3 -C 6 )cycloalkyl, (C═O) a O b (C 1 -C 6 )alkyl, or S(O) m R a ;

or a pharmaceutically acceptable salt, tautomer, or a stereoisomer thereof.

3. A compound which is selected from:

9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-amine;

9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-ol;

9-phenyl-8-(4-{[4-(4-pyridin-2-yl-1H-imidazol-1-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-amine;

9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-thiol;

3-methyl-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(chloromethyl)-9-phenyl-8-(4-{[4-(4-pyridin-2-yl-1H-imidazol-1-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-[(4-methylpiperazin-1-yl)methyl]-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

2-({[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-1H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]methyl}amino)ethanol;

8-(4-Aminomethyl-phenyl)-9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-3-ol;

1-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

4-(3-Methyl-9-phenyl-[1,2,4]triazolo[3,4-f][1,6]naphthyridin-8-yl)-benzylamine;

8-[4-(Aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-amine;

1-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine;

9-Phenyl-8-{4-[4-(5-pyridin-2-yl-4H-[1,2,4]triazol-3-yl)-piperidin-1-ylmethyl]-phenyl}-[1,2,4]triazolo[3,4-f][1,6]naphthyridine;

9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)-3-(1H-1,2,3-triazol-4-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

tert-butyl[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)

[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]methylcarbamate;

[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]methanol;

5-[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]-2,4-dihydro-3H-1,2,4-triazol-3-one;

3-(3-methyl-1H-1,2,4-triazol-5-yl)-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-imidazo[2,1-b][1,3]thiazol-6-yl-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)-3-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-imidazo[1,2-a]pyridin-2-yl-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)-3-(1H-1,2,4-triazol-5-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(1H-benzimidazol-6-yl)-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(1,5-dimethyl-1H-pyrazol-3-yl)-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-imidazo[1,2-a]pyrimidin-2-yl-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

5-[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]pyridin-2-amine;

9-phenyl-3-pyrazolo[1,5-a]pyrimidin-3-yl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(5-methyl-1H-pyrazol-3-yl)-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]pyridin-2-amine;

4-[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]phenol;

3-[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]phenol;

2-[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]phenol;

1-{4-[3-(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}piperidine-4-carboxamide;

1-[4-(3-imidazo[1,2-a]pyridin-2-yl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]piperidine-4-carboxamide;

9-phenyl-8-(4-{[4-(5-pyrazin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)-3-(1H-1,2,3-triazol-4-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrimidin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[4-(5-pyrazin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

N-[2-(4-methyl-1H-imidazol-2-yl)ethyl]-N-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}amine;

N 1 -(2-hydroxyphenyl)-N 3 -{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}-beta-alaninamide;

1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}piperidine-4-carboxamide;

5-[({4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}amino)methyl]pyridin-2-ol;

N 1 ,N 1 ,2,2-tetramethyl-N 3 -{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}propane-1,3-diamine;

3-hydroxy-2,2-dimethyl-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propan-1-amine;

2-fluoro-3-hydroxy-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propan-1-amine;

2,2-difluoro-3-hydroxy-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propan-1-amine;

2,3-dihydroxy-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propan-1-amine;

4-hydroxy-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]cyclohexanamine;

4-hydroxy-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]cyclohexanamine;

3-hydroxy-2,2-dimethyl-N-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}propan-1-amine;

3-hydroxy-2,2-dimethyl-N-[4-(9-phenyl-3-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propan-1-amine;

3-hydroxy-2,2-dimethyl-N-[4-(9-phenyl-3-pyrazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propan-1-amine;

3-hydroxy-2,2-dimethyl-N-{4-[9-phenyl-3-(1H-1,2,3-triazol-4-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}propan-1-amine;

tert-butyl {[8-(4-{[(3-hydroxy-2,2-dimethylpropyl)amino]methyl}phenyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]methyl}carbamate;

N-{4-[3-(ammoniomethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}-3-hydroxy-2,2-dimethylpropan-1-amine;

[9-phenyl-8-(4-{[4-(5-pyrazin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]methanol;

N 3 -{4-[3-(hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}-N 1 -(2-hydroxyphenyl)-beta-alaninamide;

(8-{4-[(cyclohexylamino)methyl]phenyl}-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl)methanol;

N 3 -{4-[3-(hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}-N 1 -(4-hydroxyphenyl)-beta-alaninamide;

[9-phenyl-8-(4-{[4-(5-pyridin-3-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]methanol;

1-{4-[3-(hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}piperidine-4-carboxamide;

{8-[4-(1-aminocyclopropyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanol;

1-[4-(9-phenyl-3-pyridin-4-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-{4-[3-(1-oxidopyridin-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-[4-(3,9-diphenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-{4-[3-(4-fluorophenyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}benzonitrile;

4-(9-phenyl-3-pyrimidin-4-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzylamine;

1-{4-[3-(1-oxidopyridin-2-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

5-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}yridine-2-ol;

1-[4-(9-phenyl-3-pyridin-3-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

4-(9-phenyl-3-pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzylamine;

1-[4-(9-phenyl-3-pyridin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-[4-(9-phenyl-3-pyrazin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-{4-[9-phenyl-3-(1H-1,2,4-triazol-3-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1,3-thiazol-4-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1H-pyrazol-4-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(3-methyl-1H-pyrazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(3-methyl-1H-1,2,4-triazol-5-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(1-methyl-1H-pyrazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1,2,5-thiadiazol-3-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1,2,3-thiadiazol-4-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-[4-(9-phenyl-3-pyrazolo[1,5-a]pyrimidin-3-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanamine;

{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methanol;

1-{4-[9-phenyl-3-(2,2,2-trifluoroethyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1H-tetraazol-1-ylmethyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine-3-carboxamide;

1-{4-[3-(1H-imidazol-1-ylmethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-(4-{3-[(methylsulfonyl)methyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl}phenyl)methanamine;

{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}acetonitrile;

2-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}ethanol;

N-({8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methyl)acetamide;

4-[3-(2-methylimidazo[1,2-a]pyridin-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-[4-(9-phenyl-3-pyrazolo[1,5-a]pyridin-3-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-[4-(3-imidazo[1,2-a]pyridin-2-yl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-{4-[9-phenyl-3-(4,5,6,7-tetrahydro-1,2-benzisoxazol-3-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-[4-(3-imidazo[2, 1-b][1,3]thiazol-6-yl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-{4-[3-(1-methyl-1H-imidazol-5-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-[3-(1-methyl-5-phenyl-1H-pyrazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-{4-[9-phenyl-3-(4,5,6,7-tetrahydro-1-benzothien-3-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(1-isopropyl-1H-pyrazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-(4-{9-phenyl-3-[(2S)-pyrrolidin-2-yl][1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl}phenyl)methanamine;

4-[3-(1-aminoethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-{4-[3-(1H-imidazol-2-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-[4-(3-cyclopropyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-{4-[9-phenyl-3-(trifluoromethyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(5-methyl-1H-pyrazol-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(1,5-dimethyl-1H-pyrazol-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-[3-(1H-indol-2-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylaminen;

1-{4-[3-(1-methyl-1H-imidazol-2-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(3-methyl-2H-3lambda 5 -imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-[3-(6-chloroimidazo[1,2-a]pyridin-2-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-{4-[3-(1H-benzimidazol-2-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-[3-(5-cyclopropyl-4H-pyrazol-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-{4-[9-phenyl-3-(4,5,6,7-tetrahydro-1H-indazol-3-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-[9-phenyl-3-(3-phenyl-1H-pyrazol-5-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-(4-{9-phenyl-3-[3-(trifluoromethyl)-1H-pyrazol-5-yl][1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl}phenyl)methanamine;

1-[4-(9-phenyl-3-pyrazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-{4-[3-(1-benzyl-1H-pyrazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-[4-(9-phenyl-3-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

4-[9-phenyl-3-(1-phenyl-1H-pyrazol-4-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-{4-[9-phenyl-3-(4,5,6,7-tetrahydro-2-benzothien-1-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-2-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

2-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}propan-2-amine;

1-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}ethane-1,2-diol;

4-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}imidazolidin-2-one;

(2R)-2-amino-2-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}ethanol;

(2R)-2-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}-2-(methylamino)ethanol;

1-{4-[3-(5-ethylisoxazol-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

5-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}-2,4-dihydro-3H-1,2,4-triazol-3-one;

6-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}-4,5-dihydropyridazin-3(2H)-one;

6-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}pyridazin-3(2H)-one;

N-(4-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}phenyl)acetamide;

1-{4-[3-(4-phenoxyphenyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(1H-benzimidazol-5-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

(4-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}phenyl)methanol;

4-[3-(4-cyclohexylphenyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

4-{8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}-1,3-dihydro-2H-imidazol-2-one;

1-{4-[3-(4-methyl-1H-imidazol-5-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-[9-phenyl-3-(1-propyl-1H-imidazol-4-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-{4-[3-(1-isopropyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[3-(1-butyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-[4-(3-imidazo[1,2-a]pyrimidin-2-yl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

5-({[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}methyl)pyridin-2-ol;

1-(6-methoxypyridin-3-yl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]methanamine;

N-[(2-methoxypyrimidin-5-yl)methyl]-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amine;

1-[4-(3-ethyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

1-[4-(9-phenyl-3-propyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanamine;

N-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

4-({[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}methyl)phenol;

1-[9-phenyl-8-(4-{[4-(5-pyridin-2-yl-4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl]methanamine;

9-phenyl-3-(1H-1,2,3-triazol-4-yl)-8-(4-{[4-(4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)

[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

1-{4-[3-(1H-Imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(3H-1 lambda 4 ,3-thiazol-5-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1H-pyrazol-3-yl)-2H-4lambda 5 -[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-{4-[9-phenyl-3-(1,3-thiazol-4-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

4-[9-Phenyl-3-(pyrrolidin-1-ylmethyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

1-{4-[3-(azetidin-1-ylmethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

1-({8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methyl)piperidine-4-carboxamide;

1-{4-[3-(morpholin-4-ylmethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanamine;

2-[({8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methyl)amino]ethanol;

1-(4-{3-[(4-methyl piperazin-1-yl)methyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl}phenyl)methanamine;

4-[9-phenyl-3-(piperazin-1-ylmethyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzylamine;

N-({8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methyl)-N-methylamine;

N-({8-[4-(aminomethyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-yl}methyl)-N,N-dimethylamine;

[4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanol;

{4-[3-(1-Methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}methanol;

1-[4-(9-Phenyl-3-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanol;

9-phenyl-8-(4-{[4-(4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-methyl-9-phenyl-8-(4-{[4-(4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

9-phenyl-8-(4-{[4-(4H-1,2,4-triazol-3-yl)piperidin-1-yl]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-3-ol;

1-[4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclopropanamine;

1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclo propanamine;

1-[4-(9-phenyl-3-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclopropanamine;

1-{4-[9-phenyl-3-(5,6,7,8-tetrahydro imidazo[1,2-a]pyridin-2-yl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclopropanamine;

1-[4-(9-phenyl-3-pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclopropanamine;

1-{4-[3-(1,5-dimethyl-1H-pyrazol-3-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}cyclopropanamine;

(1R)-1-[4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine;

(1R)-1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine;

(1R)-1-{4-[9-Phenyl-3-(5-pyridin-2-yl-1H-pyrazol-3-yl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}ethanamine;

(1R)-1-{4-[3-(hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}ethanamine;

(1R)-1-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}ethanamine;

(1R)-1-[4-(9-phenyl-3-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine;

(1R)-1-[4-(3-imidazo[2,1-b][1,3]thiazol-6-yl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine;

(1R)-1-[4-(9-phenyl-3-pyrimidin-2-yl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethanamine;

(1R)-1-[4-(9-Phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]propan-1-amine;

2-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]propan-2-amine;

2-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]propan-2-amine;

3-(2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)pyridine;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-5-pyridin-4-yl-2-furamide;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-5-pyridin-3-yl-2-furamide;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-5-pyridin-3-yl-1H-pyrrole-3-carboxamide;

2-hydroxy-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

tert-butyl (2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)carbamate;

4-(2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)morpholine;

2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethanamine;

4-(2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)pyridine;

2,4-dihydroxy-6-(2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)pyrimidine;

2-(2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)pyridine;

3-(2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)pyridine;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-2-pyrazin-2-ylacetamide;

3-methyl-9-phenyl-8-[4-({[(pyridin-3-ylamino)carbonyl]amino}methyl)phenyl][1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

2-(2-hydroxyphenyl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

2-(3-hydroxyphenyl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

2-(4-hydroxyphenyl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

2-(3,4-dihydroxyphenyl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-2-phenylacetamide;

3-methyl-9-phenyl-8-(4-{[(pyridin-3-ylcarbonyl)amino]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

2-hydroxy-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]benzamide;

2-(4-hydroxyphenyl)-2-methyl-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propanamide;

methyl 4-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-4-oxobutanoate;

2-hydroxy-N-(2-{[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]amino}-2-oxoethyl)benzamide;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-2-(5-phenyl-4H-1,2,4-triazol-3-yl)acetamide;

3-methyl-9-phenyl-8-(4-{[(quinolin-3-ylcarbonyl)amino]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-2-(4-oxoquinazolin-3(4H)-yl)acetamide;

N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]-2-(2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide;

8-(4-{[(1H-benzimidazol-1-ylacetyl)amino]methyl}phenyl)-3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

8-(4-{[(1H-benzimidazol-2-ylacetyl)amino]methyl}phenyl)-3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

2-(4-methyl-1,2,5-oxadiazol-3-yl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

2-(1H-indazol-1-yl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

2-(5,6-dimethyl-4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

3-methyl-8-[4-({[(6-morpholin-4-ylpyridin-3-yl)carbonyl]amino}methyl)phenyl]-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

2-(6-chloropyridin-3-yl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]acetamide;

3-cyano-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl]propanamide;

3-methyl-9-phenyl-8-(4-{[(3-pyridin-3-ylpropanoyl)amino]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{[(pyridin-3-ylacetyl)amino]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

9-phenyl-3-pyrazolo[1,5-a]pyrimidin-3-yl-8-(4-{[(pyridin-3-ylacetyl)amino]methyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

N-(3-hydroxy-2,2-dimethylpropyl)-N-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl) benzyl]acetamide;

N-(3-hydroxy-2,2-dimethylpropyl)-N-{4-[3-(1-methyl-1H-imidazol-4-yl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]benzyl}-2-(4-oxoquinazolin-3(4H)-yl)acetamide;

tert-butyl {2-[[4-(3-{[(tert-butoxycarbonyl)amino]methyl}-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzyl](3-hydroxy-2,2-dimethylpropyl)amino]-2-oxoethyl}carbamate;

3-methyl-9-phenyl-8-(4-{1-[(pyridin-3-ylacetyl)amino]cyclopropyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

3-methyl-9-phenyl-8-(4-{1-[(quinolin-3-yl carbonyl)amino]cyclopropyl}phenyl)[1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

N-{1-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]cyclopropyl}-2-(4-oxoquinazolin-3(4H)-yl)acetamide;

3-(1-methyl-1H-imidazol-4-yl)-9-phenyl-8-(4-{1-[(pyridin-3-ylacetyl)amino]cyclopropyl}phenyl) [1,2,4]triazolo[3,4-f]-1,6-naphthyridine;

N-{(1R)-1-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}-2-pyridin-3-ylacetamide;

N-{(1R)-1-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}acetamide;

N-((1R)-1-{4-[3-(hydroxymethyl)-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl]phenyl}ethyl)-2-pyridin-3-ylacetamide;

N-{1-methyl-1-[4-(9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}acetamide; and

N-{1-methyl-1-[4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]ethyl}acetamide;

or a pharmaceutically acceptable salt or stereoisomer thereof.

4. A pharmaceutical composition comprising a pharmaceutical carrier, and dispersed therein, a therapeutically effective amount of a compound of claim 1 .

Assignments (3)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
CHANGE OF NAME Recorded Aug 29, 2012
From: SCHERING CORPORATION
To: MERCK SHARP & DOHME CORP.
Reel/Frame 028866/0511 →
MERGER Recorded Aug 27, 2012
From: MERCK SHARP & DOHME CORP.
To: SCHERING CORPORATION
Reel/Frame 028850/0515 →